You Made It Weird with Pete Holmes

Episode: Reggie Watts Returns

Release Date: October 30, 2024
Guest: Reggie Watts

Episode Overview

This episode of You Made It Weird marks the long-awaited return of multi-talented musician and comedian Reggie Watts, who originally performed the show’s theme song over a decade ago. Pete and Reggie dive deep into everything from creativity and playfulness to AI, consciousness, psychedelics, paradox, and the search for meaning. The conversation traverses philosophy, technology, comedy, identity, and ways to live more freely and presently.

The episode is rich with spontaneous humor, tangential stories, and profound reflections, all colored by the duo’s unique rapport and playful energy.

Key Discussion Points & Insights

1. Reunion Vibes, Whimsy, and Reggie’s Creative Approach

• Theme song history: Reggie reminisces about writing the "You Made It Weird" theme song 10+ years ago ([00:15]).
• Performing with play: Pete reflects on how Reggie’s performances embody creative freedom and playfulness, contrasting absorbing media with making it ([05:26]).
• Improv is the secret: Reggie shares, "Improvisation is kind of like, it makes the mundane more fantastic" ([13:43]).

2. The AI Zone: Animals, Capitalism, and Cultural Absurdities

• AI won’t get us: Pete and Reggie muse on how artificial intelligence wouldn't fathom human practices like animal cruelty, borders, or world hunger ([11:06]–[12:11]).
  • Pete: “I think AI just won’t understand it. … Some of the great cultural myths, the brutalities we just accept.”
• Capitalism and power: The conversation critiques our systems, from land ownership to endless growth, suggesting our culture is filled with irrational inherited norms ([30:26]).

3. Improvisational Living and Flow

• Pete references Reggie's old advice: “Just drive home a different way. … Your brain will go like—thank you.” ([14:04])
• Mini decisions matter: The importance of making small, out-of-routine choices to spark creativity and presence ([15:05]).
• Match Point analogy: Pete uses a tennis metaphor—life pivots on little decisions, like whether you get out of bed ([14:59]).

4. Music, Hyperpop, and the Internet’s Influence on Art

• Hyperpop explained: Reggie details the genre's ADD-editing, queer/trans roots, and constant stimulation—mirroring internet-era brains ([17:53], [20:00]).
• Jake Lodwick & Vimeo: Early internet’s influence on Reggie’s sensibilities—“What I was doing mimicked the brain that we were starting to get from interacting with the internet” ([23:13]–[25:20]).

5. Tech Metaphors and Evolution

• Operating systems: The duo discusses how digital metaphors (desktop, file, etc.) derive from the physical world, and our brains have evolved to organize information like computers ([25:45], [26:09]).
• Designing from scratch: Pete admires Google’s “what if email didn’t exist?” design mentality—mirroring Reggie’s improv philosophy ([28:00]).

6. Philosophy, Consciousness, and Psychedelics

• Simulations, pain, and paradox: Deep dives into whether life is a simulation, the necessity of pain, and meaning—
  • Pete: “A thing elected to become two things, and the sacrifice...is pain and the gain is intimacy and creation” ([50:05]).
• Ketamine insights: Both share transformative psychedelic experiences, especially ketamine’s ability to create “paradox states” where the experiencer and observer merge ([53:24], [54:13]).
• On delightfully irrelevant existence: “So many people come back from psychedelics and say ‘it’s a big void’—but you missed the blissful void, the joyfully meaningless” ([51:54]).
• Reggie, on ketamine: “You are able to…be consciousness. … Once you’re quantumly entangled between an observational and experiential point, that’s what ketamine is—the liminal space.” ([54:36])

7. Loops, Egos, and Letting Go

• Breaking habit loops: Reggie sees depression as a “loop,” and talks about ketamine enabling a step outside those ruts ([57:44]).
• Bag analogy: Psychedelics help us to “put the bag down”—whether that’s need for approval, anxiety, or pain ([64:02]).
• Ego death: Facing the “moth in the flame” of ego dissolution—“We want peace and liberation and infinite spacious… but we don’t get to go—Reggie doesn’t get to go” ([66:15]).

8. Oneness, Love, and Recognition

• The me, not me: Both discuss mystical experiences of encountering the “me that is not me,” profound unity, and the spiritual heart at the core of all things ([72:41]–[74:39]).
• Pete: “When I try to love Reggie…when I recognize it’s just me.”
• Shared dream metaphor: Reality as a co-generated dream, not just “Reggie’s dream” ([87:43]).

9. Power, Addiction, and Compassion

• Addiction to power: The pathology of hoarding money/power is compared to a heroin addiction, with side-effects for everyone else ([89:00]).
• Sufi/NatAm mythologies: Reggie references cultural stories about spiritual “infections” or greed, as part of humanity ([91:24]–[92:13]).

10. Practical Wisdom for Artists/Performers

• Pressure and nerves: How Reggie handles nerves and structure, especially in high-pressure settings like TED, by trusting in play and letting the “thing” emerge when on stage ([104:14]–[108:51]).
• Advice to artists: “Don’t fixate on every show… You’ve got thousands of shows to do” ([102:09]).

11. Philosophical Closure: Actors, Characters, and Forgiveness

• Everyone’s playing a character: Reggie aims to “speak to the actor, not the character”—useful in relationships and conflicts ([125:22]).
• Mercy over forgiveness: Pete distinguishes between the two—“Mercy just is a bug zapper…forgiveness goes, ‘you were a little late, but it’s okay.’” ([100:07])
• Let things glide: Use meditation or presence so “life leaves no trace”—let difficult moments move through you ([129:53]).

Notable Quotes & Moments

Creativity, Play, and Improvisation

• Reggie, on improv:
  “Improvisation is kind of like, it makes the mundane more fantastic.” ([13:43])
• Pete, on routine:
  “Every time that you make that extra effort…your brain will thank you for it.” ([14:16])

AI & Human Absurdity

• Pete:
  “I think AI just won’t understand it… One of the great cultural myths—killer be killed. But now we live in the modern world and you’re gonna wake up this intelligence that’s gonna be like, ‘What?’” ([11:07])

On Psychedelic Insights & Paradox

• Pete:
  “So many people come back from psychedelics and they’re like, ‘it’s a big void,’ and I’m like you missed the key part…the blissful void…the joyfully meaningless.” ([51:54])
• Reggie:
  “You are able to…be consciousness. You are two beings: you are aware of something, and you’re aware of yourself while being yourself.” ([54:13])

Art, Performance, and Pressure

• Reggie:
  “I gotta trust my instincts. … Be the person that you laugh with when you’re in your room playing by yourself.” ([105:56])
• On nerves and structure:
  “If I have to remember something to do on stage, then I’m going to be disappointed that I’ve not done it if I’ve forgotten it.” ([107:09])

Oneness and Self-Love

• Reggie (on a mushroom trip):
  “I was just surrounded by this presence. … I was like, ‘Oh my God, I haven’t seen you in so long. I miss you so much.’ … This is me, but this is not me.” ([72:41])
• Pete:
  “In the word ‘me,’ there’s an acceptance… If everyone felt that way, we would feel we.” ([73:12])

Mercy

• Pete:
  “Mercy beats forgiveness, because mercy doesn’t even ask what you did. Mercy just is a bug zapper.” ([100:07])

Notable Comic Moments

• Dumpster K-hole: Reggie’s story of tripping on ketamine next to a dumpster, finding beauty in every circumstance ([60:55]).
• DIY sound effects: Reggie and Pete swapping spit-based sound effects and impressions ([83:05]–[84:01]).
• Cajun food bit: Their riff on Cajun food turns into a pun-filled tangent ([112:06–113:38]).

Important Timestamps

| Time | Segment | |----------|------------------------------------------------------------| | 00:15 | Pete’s intro: Reggie’s role in the show’s theme song | | 05:26 | On creativity, play, and the value of making vs. watching | | 11:06 | The AI won’t get us: animals, capitalism, and human myths | | 13:43 | Reggie on improvisation making the mundane fantastic | | 20:00 | Hyperpop and ADD-music; the influence of internet culture | | 28:00 | “Invent email”: rebuilding from scratch, breaking orbits | | 50:05 | “A thing became two”: pain, joy, and the cost of being | | 53:24 | Ketamine and paradox, the observer and experiencer | | 64:02 | Psychedelics and putting down ‘the bag’ (burdens) | | 72:41 | Mushroom trip: meeting “the me, not me,” soul-level unity | | 89:00 | Addiction to power vs. compassionate living | | 102:09 | Advice: Don’t fixate—life is many shows | | 125:22 | Characters & actors: relating from the ‘actor’ not character| | 132:12 | Reggie sings the theme song live |

Tone & Flow

This episode is a masterclass in conversational philosophy: warm, honest, irreverent, metaphysical, and sometimes trippy. There’s constant interplay between comedy and wisdom, with both Pete and Reggie allowing for vulnerable, spontaneous reflection, uncensored tangents, and mutual encouragement. The tone is introspective but often silly, holding lightness alongside depth.

For New Listeners

If you haven’t heard this episode, expect a free-wheeling, mind-expanding chat with improvisational detours, profound insights, and lots of laughter. The conversation is both accessible and profound, making space for the spiritual, the absurd, and the everyday challenges of being a person, artist, or even just a consciousness in this weird world.

Closing

Reggie closes, in his signature playful musical style, riffing on the theme song (“You made it weird…You made it weird… You made it weird!” [132:12]) and the two reflect on the spirit of “keeping it crispy”: embracing presence, imperfection, and the joy of connection.

“You have made it weird. Starring…you made it crispy. That’s it. We did it.” – Reggie Watts ([133:21])